Q4(e). Three rearrangement and condensation sequences
Complete (i) the drawn cyclic benzyl ammonium salt with NH₂⁻ in NH₃; (ii) salicylaldehyde + ethyl acetoacetate/piperidine, then PhCHO and bromine; (iii) Ph₂C(OH)C(OH)Me₂ with AcOH/trace H₂SO₄ versus cold H₂SO₄. [structure of the ammonium salt given in the paper]
Model answer
The free solution for 2021 answers questions 1, 2, 3, 5 and 6, the ones picked in its time plan. This part is not answered on the site yet. New answers are announced on Telegram.
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CoversStevens rearrangementKnoevenagel condensationcoumarin synthesispinacol–pinacolone rearrangementmigratory aptitude
All parts of Question 4
- 4(a)(i) Cyclopentadiene and methyl acrylate5 marks
- 4(a)(ii) Tetraphenylcyclopentadienone cycloaddition5 marks
- 4(b) Oxidation and oxidative cleavage5 marks
- 4(c)(i) Substitution versus elimination of a primary bromide5 marks
- 4(c)(ii) Alcohol to chloride with retention5 marks
- 4(d)(i) Regioselective hydration of allylbenzene5 marks
- 4(d)(ii) Nucleoside and nucleotide structures5 marks
- 4(e) Three rearrangement and condensation sequences5 marks